Chlorotrimethylsilane → N,1,1,1-Tetramethyl-N-phenylsilanamine

HRID 1192997Notes

Reaction equation

HRID 1192997 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.Cl[Si:15]([CH3:18])([CH3:17])[CH3:16]>C(OCC)C>[CH3:16][Si:15]([CH3:18])([CH3:17])[N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7515N-MethylanilineHCID 178418339Butyllithium

Product 1

HCID 12418931N,1,1,1-Tetramethyl-N-phenylsilanamineYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Step 1—To a stirring solution of N-methylaniline (80 g, 0.75 mol) in diethyl ether (600 ml) cooled at −78° C. was added n-butyl lithium (2.4 M in hexanes, 342 ml, 0.82 mol) keeping the temperature below −60° C. The resulting slurry was stirred for 1 hour then chlorotrimethylsilane (114 ml, 0.90 mol) was added while keeping the temperature below −70° C. The reaction was allowed to warm to room temperature overnight then filtered to remove the precipitated white solid. The filtrates were concentrated in vacuo then distilled under high-vac to yield the N-trimethylsilyl-N-methylaniline (126 g, 94%) as a colorless/straw colored liquid: b.p. 48° C./0.6 mmHg; 1H NMR (CDCl3) 0.33 (s, 9H), 2.95 (s, 3H), 6.85 (t, 1H, 7 Hz), 6.94 (d, 2H, 8 Hz), 7.27 (t, 2H, 9 Hz).

Workup

  1. customthe temperature below −60° C
  2. customthe temperature below −70° C
  3. filtrationthen filtered
  4. customto remove the precipitated white solid
  5. concentrationThe filtrates were concentrated in vacuo
  6. distillationthen distilled under high-vac

Sources & evidence

ORD record
ord-16475e8d963843b89e2888e85f154c81
Source dataset
uspto-grants-2014_03
Patent number
US08680332B2

Reaction notes

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